The largest city in Oregon, Portland is renowned for a variety of things, not least its “weirdness.” For one, it’s one of the world’s most environment-conscious cities and a counterculture hotspot in the United States. This is a city of hipsters and cyclists, nature conservation and sustainable farm-to-fork dining. It has one of America’s best public transportation systems and more than 10,000 acres of public parks. Despite its lack of major architectural landmarks and historic sites, there are still a ton of fun things to do in Portland, Oregon.
If you’re looking for fun things to do in Portland, the city will definitely deliver. Don’t expect any traditional urban activities here, though. “Keep Portland Weird” is a message you’ll notice all over the city, a characteristic the locals are extremely proud of.
Instead, prepare to immerse yourself into a few thriving subcultures, enjoy some truly beautiful natural areas, and indulge in world-class food and drinks during your stay in Portland.
Enjoy the view From Pittock Mansion
Soaring 1,000 feet above downtown Portland in the West Hills, Pittock Mansion is one of Portland’s few architectural attractions. Originally built for Oregonian publisher Henry Pittock and his wife in 1914, this French Renaissance-style mansion is now open to visitors. It’s an impressive house, but the real treat lies behind it.
From the back garden, the view overlooks pretty much the entire city of Portland, including Mt. Hood towering in the distance. Super-accessible, it’s a marvelous place to watch the sunrise or sunset.
Go for a walk in Forest Park
Pittock Mansion lies at the southern edge of Forest Park, at the end of the 30-mile Wildwood Trail. You can either drive or hike up to the mansion. The short hike from Lower Macleay Park, along Balch Creek, past the Stone House ruins and up the hill is absolutely wonderful.
It’ll give you a first taste of the gorgeous forest scenery of the Pacific Northwest. As you walk underneath moss-covered trees and alongside a bubbling stream, you won’t feel like you’re actually still within Portland. It’s a popular place to escape among Portlanders. Forest Park is the largest urban park in the U.S.
Have a dozen Voodoo Doughnuts
A Portland icon, Voodoo Doughnuts has gotten national attention lately. This results in long waits outside just to grab a box of donuts, but it’s one of those typically Portland things to do that’s almost mandatory for an all-round Portland experience.
Voodoo Doughnuts is in the Old Town district near the waterfront, which is also (in)famous for its happening nightlife.
Get lost in Powell’s Books
This is one of those fun things to do in Portland that you can literally only do in Portland. Powell’s Books, located in the hip Pearl District, is the world’s largest independent used and new bookstore. It occupies an entire city block, including several stories. Its more than 1 million books are divided into no fewer than 3,500 different sections.
If you don’t want to get lost, you’ll literally need a map to navigate the nine color-coded areas (maps are available).
Visit The International Rose Test Garden
Portland’s dry, warm summers and cool, wet winters are absolutely ideal for growing roses. The city’s nicknamed the “City of Roses” for a reason. The best place to see what this is all about is the International Rose Test Garden in Washington Park, the oldest continuously operated public rose garden in the U.S.
A wander through this multi-colored garden is one of the most fun things to do in Portland. Prime rose-viewing is from May to September.
Watch the sunset from atop an extinct volcano
While the active volcanoes near Portland, such as Mount St. Helens, Mount Adams and Mount Hood, are well-known, the fact that there are a number of extinct volcanoes within the city limits is not. There are at least three volcanic cinder cones in East Portland, their summits all home to public parks.
The most popular one is Mt. Tabor, which offers fine views of both Portland and Mount Hood. A less-known place, however, is Rocky Butte, located near the intersection of I-84 and I-5. The top overlooks the Columbia River, the PDX airport and Mount St. Helens to the north and offers clear views of Mount Hood. It’s a great spot to watch planes take off and land.
My personal favorite, on the other hand, is Powell Butte, far in the southeast of Portland. This nature park has several nice hiking trails, while its summit meadows provide panoramic views of the mountains.
Bike across a bridge
Situated at the confluence of the Willamette and Columbia Rivers, Portland has more than its fair share of bridges. In fact, another of its nicknames is “Bridge City,” sometimes also “Bridgetown.” There are no fewer than 14 bridges in Portland, 12 across the Willamette and 2 across the Columbia toward Washington State.
Grab an orange bicycle at one of the many bike-share locations (known as Biketown PDX) across the city and pedal your way across a bridge. It’s one of those really fun things to do in Portland on a sunny afternoon. Recommended bridges are the Hawthorne Bridge, Tilikum Crossing Bridge and the engineering masterpiece that is the Steel Bridge.
here’s an ungodly number of strip clubs in Portland, from classy to sassy. No other city in the United States has such a high number of strip clubs per capita. You’ll find them all over, from the outskirts to the heart of the city center.
So, if you’re into that sort of stuff, a strip club visit is without question one of the most fun things to do in Portland. Some of them will surprise you, for sure. There’s an option for everyone, with themes that range between dive-bar vibe, rock ‘n’ roll, burlesque and hip hop. And it wouldn’t be Portland if there wasn’t a vegan strip club, too!
Grab lunch at a food cart pod
Another one of Portland’s typical features is its countless street food carts. They’re usually gathered together in so-called food cart pods. One of the most popular ones is in a block between SW Washington and SW Alder Streets in downtown Portland. You’ll find everything from grilled cheese to Vietnamese, Middle Eastern and Egyptian food.
Walk the Eastbank Esplanade
Extending from 1.5 miles from the Hawthorne Bridge northward to the Steel Bridge, the Vera Katz Eastbank Esplanade is a paved walking and biking path along the eastern shore of the Willamette River.
It offers superb views of the Portland skyline and has several facilities, including viewpoints, a floating boardwalk, a canoe launch, boat dock and public art. There are connections to the East Portland neighborhoods and across the river to Gov. Tom McCall Waterfront Park.
Explore the thriving craft beer scene
Home to no fewer than 70 breweries, Portland is one of the world’s beer capitals. If you’re a lover of the golden liquid, going on a craft beer tour is one of the most fun things to do in Portland for sure. Most of the breweries are located in the expansive eastern part of the city, east of the Willamette River, but there are a few excellent ones in the Pearl District and Northwest as well.
I personally recommend Back Pedal Brewing (they also have beer-bike tours!), Upright Brewing, Base Camp Brewing Company and Culmination Brewing. There is, however, a huge offering of craft beer in Portland. Feel free to do your own research—there are veritable gems in this city.
Go for a day trip
There aren’t only fun things to do in Portland itself, though. The great thing about this city is its proximity to some of North America’s most spectacular landscapes. Rent a car and head to the waterfall-filled Columbia River Gorge or go hiking (or skiing) in Mt. Hood National Forest. Alternatively, the Oregon Coast boasts such natural beauty that it’ll overwhelm even the staunchest city dweller.
Across the Washington border, you’ll find sensational landscapes around Mount St. Helens and, further north, in world-class Mount Rainier National Park.